The teaching and learning of long division at the elementary level and beyond has presented a longstanding challenge for teachers and students alike. As mathematics teacher educators and as a specialized educator, we address the issue by analyzing some of the challenges involved in the teaching and learning of long division – particularly focusing on students who struggle in mathematics. Our inspiration comes from two shared experiences. First, a lesson taught by one of our graduate level, in-service special education teachers inspired us to consider how other teachers could consider teaching division by using an area model. The lesson that began our initial conversations will be shared later in this article to exhibit one teacher’s use of area in teaching division in an interactive manner. Second, these conversations led to our collaborative work on a book chapter that centered on specialized mathematics education (Pratt, Richardson, & Kurtts, in press) In our chapter we focused on the significance of epistemological perspectives and how imagery relates to effective mathematics teaching and learning